Shelter Island Holidays from £826
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £335 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Shelter Island Holiday
Lock in a Shelter Island holiday package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighbourhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organising a tailored Shelter Island holiday is a cinch with Expedia.
Top Shelter Island Flight + Hotel Deals
Park Central Hotel New York
Reviewed on 10 Feb 2026
Sanctuary Hotel New York
Reviewed on 8 Feb 2026
Comfort Inn Manhattan - Midtown West
Reviewed on 31 Jan 2026
1 Hotel Brooklyn Bridge
Reviewed on 29 Jan 2026
NobleDEN Hotel
Reviewed on 10 Feb 2026
Where to stay in Shelter Island
Silver Beach
While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.
Shelter Island Beach Holiday
There's nothing that can beat a Shelter Island holiday. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favourite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 1 mile from downtown. However, you'll also discover a fantastic range of Shelter Island holiday deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.
Shelter Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,350 |
Max Temp Winter | 4ºC |
Max Temp Summer | 24ºC |
Top Sights | East Hampton Main Beach, Wolffer Estates Vineyard and 67 Steps Beach |
Top hotels in Shelter Island
Gurney's Montauk Resort & Seawater Spa
Room was spotless, staff were great and the resort is top notch!!
Reviewed on 2 Feb 2026
Sound View Greenport
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on 10 Jan 2026
Montauk Manor
The room was lovely, the little kitchenette is great. Very quiet and I love the balcony. The staff are great and the restaurant staff at Montis are fantastic
Reviewed on 1 Feb 2026
Popular places to visit
Shelter Island Historical Society
You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.
Havens House
You can spend an afternoon studying the exhibits at Havens House during your travels in Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
